Stability studies on trans-rosmarinic acid and GC–MS analysis of its degradation product

The stability of trans-rosmarinic acid (trans-RA, an important phenolic compound with anti-oxidant, anti-inflammatory, anti-bacterial, and anti-viral properties) exposed to different stress conditions (daylight, higher temperatures, different solvents, and humidity) was investigated. Gas chromatography–mass spectrometry (GC–MS) was used to analyse the degraded samples, and structural identification of degradation products was assigned based upon MS fragmentation pattern. The GC–MS method was validated in terms of linearity, precision as repeatability, accuracy, limit of detection (LOD), limit of quantitation (LOQ) and recovery. The stability experiments were performed on pure trans-RA and on trans-RA present in commercially available rosemary extract. The cis-isomer of RA was the only degradation product. The results showed that trans-RA was readily isomerized into its cis-form within a few hours when dissolved in ethanol, methanol or tetrahydrofuran, and exposed to darkness or daylight at different temperatures. Isomerization took place to a greater extent in protic than in aprotic solvents. Trans-RA in the solid state was found to be stable for up to three months under all tested conditions. The described GC–MS method was also applied to the determination of trans-RA in eight different species of Lamiaceae family.